Miles Davis’ First Great Quintet was assembled in 1955—a pivotal year for the trumpeter and bandleader. Following a triumphant set at the Newport Jazz Festival, Davis was at the top of his game, and enjoying newfound recognition by industry leaders, critics, and fans alike. With a lineup that featured pianist Red Garland, bassist Paul Chambers, drummer Philly Joe Jones and a relatively unknown tenor saxophonist named John Coltrane (replacing Sonny Rollins), the unit became the dominant small jazz group of the late 1950s and helped define the hard-bop genre.

Over the course of a year—from November 1955 to October 1956—the quintet recorded three exceptionally productive sessions with famed engineer Rudy Van Gelder, simulating nightclub sets at Van Gelder’s Hackensack, New Jersey studio. The resulting 32 tracks would make up five complete and significant albums: the quintet’s 1956 debut release, Miles: The New Miles Davis Quintet, Cookin’ (1957), Relaxin’ (1958), Workin’ (1959), and Steamin’ (1961). The quintet’s recording of “’Round Midnight” would represent this ensemble’s lone contribution to the album Miles Davis and the Modern Jazz Giants (1959).The majority of these tracks are pop and jazz standards, along with several original compositions from Davis. Highlights include a rendition of Thelonious Monk’s “’Round Midnight,” which Davis would adopt as a signature tune, a scorching drum solo from Jones on “Salt Peanuts,” Davis’ exquisite use of the Harmon mute on the intimate ballads “My Funny Valentine” and “It Never Entered My Mind,” Garland’s inspiring solo on “If I Were a Bell,” and a standout performance from the rhythm section on “Blues by Five.”

The Legendary Prestige Quintet Sessions was originally released as a CD box set in 2006, garnering wide critical acclaim. JazzTimes wrote that “To sit down with the 32 [tracks], from “Stablemates” to “My Funny Valentine,” is to fall in love all over again with irreplaceable music whose magic is utterly manifest yet elusive of description.” AllMusic proclaimed, “Miles freaks…will have to have this,” while PopMatters declared the collection to be “Perfect.”